Yarn conditioning process and the product thereof



Patented Aug. 19, 1941 UNITED STATES YARN CONDITIONING PROCESS AND THE PRODUCT THEREOF James G. McNally and Joseph B. Dickey, Rochester, N. Y., assignors to Eastman Kodak Company, Rochester, N. Y., a corporation of New Jersey No Drawing.

13 Claims.

This invention relates to the conditioning of textile yarns and more particularly to the conditioning of filaments and yarns composed of organic derivatives of cellulose such as cellulose acetate, cellulose propionate, cellulose acetate propionate, and cellulose acetate butyrate, to render them more amenable to textile operations such as knitting and the like.

As is well known in the manufacture of yarns,

, particularly those composed of or containing celcilitate handling in such operations as spinning,

twisting, winding and reeling. It is also necessary to treat yarn to adapt it for use as warp or filling or for the manufacture of various types of knitted fabrics. In knitting, it is particularly important that the yarn be soft and pliable in order that it may conform readily to the contour of the needles and thus produce a closely knit fabric free from such defects as stitch distortion, pin holes, laddering, and the like.

Heretofore it has been proposed to employ softening agents such as polyhydric alcohols and similar agents as ingredients of yarn conditioning or lubricating formulas, generally in connection with mineral, animal or vegetable oils. It has been found, however, that most of the known softening agents and thewarious formulas containing them have certain drawbacks, one of the most serious of which is high vapor pressure, and in some casestoo drastic a solvent action on the yarn. Many of such agents possess slight or insufficient solvent power for the lubricants with which they are used, and it is accordingly necessary to employ blending agents or emulsifying agents in order to obtain operable yarn treating formulas. In addition, many of the known softening and lubricating agents are insuihciently soluble in water to permit satisfactory removal by aqueous scour baths.

This invention has as its principal object to provide an entirely new class of yarn conditioning agents which are particularly adapted for the treatment of yarns composed of or containing organic derivatives of cellulose and capable of lubricating, softening, deelectrifying and otherwise rendering such yarns more amenable to knitting and other textile operations. A further and specific object is to provide a class of conditioning agents which augment or assist the lubricating action of various lubricants when applied to Application December 1'7, 1938, Serial No. 246,518

such yarns. A still further object is to provide yarn softening and lubricating formulas which can be readily removed from the yarns by the usual scour baths. A still further object is to provide an improved method for the conditioning of yarns, particularly those composed of or containing organic derivatives of cellulose such as cellulose acetate, whereby the yarn is rendered soft and pliable and capable of employment in a variety of textile operations where complicated designs or stitches are employed. Another object is to provide an improved type of yarn which is especially amenable to textile operations including circular knitting, weaving, spinning, the manufacture of cut staple fiber, and the like. Other objects will appear hereinafter.

These objects are accomplished by the following invention which, in its broader aspects, comprises the discovery that the salts of ketonic amines having the general formula:

a B. s' c R1 R 1' c where :1: is 1 or more; y is 1, 2, etc.; a is 1, 2, etc.; A is 1, 2, etc.; 13 is 0, 1, 2, etc.'; R and R are substituents selected from the group consisting of 30 hydrogen, substituted and unsubstituted alkyl,

cycloalkyl and heterocyclic groups, may be used as yarn conditioning agents. In the system morm we may have branched chain systems.

The structure of the salts is represented by the formula:

-N- -R .Ac

where Ac is a monoor poly-functional organic or inorganic acid.

We have found that these compounds may be used as yarn conditioning agents, with'or without the addition of animal, mineral, or vegetable oils, in the treatment of yarns composed of or containing organic derivatives of cellulose.

-' The amines from which the salts above referred to are derived, may be prepared by the method described in the following references: Monatsh. 24, 773, 25, 135, Ann., 361, 96, 367, 15, Compt. Rend. 142, 215, Ber. 28, 161.

These salts are preparedin the usual manner, that is, by neutralizing the base with the desired acid or acids with or without a solvent. If desired, an excess of the base or of an acid or acids may be employed.

In accordance with the invention these compounds may be applied directly to the yarn during or after spinning, or may be added to the spinning solution itself. We have found that these compounds have exceptional solvent powers which enable them to dissolve mineral oils and blown and unblown, drying and semi-drying, vegetable and animal oils and accordingly they may be, and preferably are, employedas ingredients of yarn conditioning or lubricating formulas. I We have also found that the above mentioned compounds are particularly valuable as anti-static agents when applied to filaments, threads, fabrics, etc., composed of or containing organic derivatives of cellulose, such as cellulose acetate, cellulose propionate, cellulose acetate butyrate, and the like, and to textile materials in general.

In the following examples and description we have set forth several of the preferred embodiments of our invention, but they are included merely for purposes of illustration and not as a limitation thereof.

Our invention will be more readily understood by reference to the following examples in which typical applications of the invention are set forth.

Ewample 1 Diaoetoneamine oleate o-o'm-o -CH8 C H a N Haoleic acid is applied to textile materials (silk, cottomwool, viscose, cellulose acetate, etc.) by means of a bath, wick, roller, spray, etc. to facilitate their knitting, weaving, spinning and the like. Yarns lubricated with this compound are of special value in the preparation of cut staple fibers. These fibers may be oiled before or after cutting.

Example 2 and applied to textile materials such as silk, wool, cellulose acetate, etc. as described in Example 1. If the yarn is intended primarily for knitting, the amount of conditioning liquid applied may vary from 4-25% by weight of the yarn and if for weaving between 1-5% by weight of the yarn.

Cellulose acetate filaments treated as described are quite soft and pliable and give improved results in various textile operations such as weaving, knitting, etc. and especially in the production of cut staple fibers.

Other examples of yarn conditioning compositions which may be applied to various types of yarns, particularly those composed of or containing cellulose acetate, cellulose acetate propionate, cellulose acetate butyrate, and similar cellulose organic acid esters in accordance with our invention and which render such yarns soft and pliable and especially well adapted for various textile operations, particularly knittin are as follows:

Example 3 Parts p-Ethylaminomethylpropyl ketone tetrahydrofurfuryloxy acetate p-Diethylamino methyl decyl ketone tetrahydrofuroate on; om out-0H, 2

.H0C0CH B,

o Blown olive oil 60 p-Methoxy ethyl succinate 38 N.HOCO--CHzO-CH3 N 5 01H; CzHs CaHs CzHs Neats-foot oil Ezample 6 Parts ,B,fl-Diethanolamino dilauryl ketone sulfate C H -CHCHz-C-CHr-CH-CQE: 5

o N(C1H40H)2.H:SO4 N(C1H4OH)| Blown neats-foot oil 95 Example 7 Parts p-Piperidino ethyl ketone phosphate onion, H H CHr-CH: CH: -o'oHr-o0-oH,-g-N CH1. 2

CHr-CH: CHr-CH3 HaPOl Water 1 Glycerol methyl ethyl ketone 70 Sperm oil 27 Example 8 Parts Mono-cetyl phosphate of /CH2 CH) N\ /CH: 02H; CHr-CH:

C-CH:8C3H1 CH3 Blown sperm oil 99-95 2,2ca,oa1 3 Example 9 Farts Example 16 Diethyl phosphate salt of In a 20% acetone solution of cellulose acetate CHFCH, are dissolved 1-5% by weight of one or more of CH the compounds claimed in this specification. The I 5 acetone solution is then extruded into an evapl i r- 2 orative atmosphere and the filaments thus produced are wound or twisted and wound. I! de- 0 H 0 sired the filaments produced by this process are e oiled with any of the combinations of lubricants Mineral 011 10 or lubricants plus conditioning agents previously Diethylene gly o dltetrahydmful'oate 18 described. Filaments thus prepared are of par- Emmfle 10 P ticular value in the preparation of cut staple arts fibers. Cetyl sulfate Sal 0! Any of the above compositions may be applied CH: to the yarn intended for use in circular knitting by means oi? a bath, wick, spray, roller, pad or any suitable means. The amount of condition- NH 1'5 ing liquid applied may vary between 5-25% by OH,- H H: weight 0!. the yarn. Usually, however, the 20 amount of conditioning liquid applied is about 10-15% by weight of the yarn. Yarn comgglfg zfgigfi gflag g g; "o posed of cellulose acetate conditioned as described above gives excellent results when used 3141113116 11 in the circular knitting process.

' Parts As will be apparent from the above examples 'Ieaseed oil 25 and description the conditioning agents of our Dl-fi-methoxyethyl 811001118139 invention may be applied by a wide variety of o H methods.- For example, we may employ the agent as an ingredient of the spinning dope from (EHPNIFILOH salt 0 CHEM) which the filaments are formed, the amount oi! H the agent so employed depending upon a num- CHHCHI CHaCH:..L- 5 her of factors, such as the particular cellulose 433F511 derivative used in making the yarn, the solvent or solvent combination used in making up the Example 12 spinning-solution, and the, degree of softness or I Parts pliability desired in the yarn, etc.

water o 0 If the conditioning agent is to be applied to m, 5 the yarn after spinning, this may be done by CH CH. 40 bringing the yarn in contact with a wick, roll,

I\ or felt wet therewith, or the liquid may be ap- (PCHPCP'CHPC lactate plied by immersion, spray, or otherwise. The on, CH: particular point at which the liquid is applied N-(CaHiOH): N-(CsELOE): a vary- It be g? 5 e yarn inside or outside he spinning ca ne Tetrahydmmrfml tetmhydmfumne 5 between the guide and godet roll, between the Emmple 13 godet or other roll or guide and the point of Part5 winding .and/or twisting. In some cases, the water 70 liquid may even be applied to the yarn after water Soluble cellulose 95991 winding onto cones, spools, bobbins, or the like Summated olive 5 or by the so-called bobbin to bobbin method. Pmsphated blown (live on In the case of staple fiber manufacture, the cm liquid may be applied to the yarn prior to, or

after cutting into staple lengths. cm CHPCH: The amount of the agent so employed will vary I 20 widely depending upon the results desired, the

specific nature of the material to which the agent onr-cfis is applied, the use to which the yarn is eventually Emmple 14 to be put and other factors. For example, in a e Parts given case where a cellulose organic acid ester Blown neats-foot 011 -9 yarn such as a. yarn composed of cellulose acetate, is intended for knitting, about 4 to 25% or Q 1 more by weight, based on the weight of the dry yarn, may be satisfactory, while if the yarn is on. CH; intended for weaving, the amount may vary be- E mp e 15 1 tween about 1- and 5%. om Although in the above examples we have rediglycofimmsm 5 r d primarily to yarn re -tins c p si n ON containing only the conditioning agent and an oil, other ingredients such as solvents, non-sol- 0 a vents, emulsifying agents, blending agents and Blown olive oil 90 the like, may be added withinthe scope of our Tetrahydrofurfurylamine tetrahydroiuroic invention. Likewise, various dyes or other colacid sa t 5 oring matter may be included in case it is desired to permanently or fugitively tint or dye the material undergoing treatment.

Although we have found it convenient to illustrate our invention by reference to compositions containing. specific percentages of the various ingredients, these percentages may vary widely depending upon the particular purpose for which the composition is intended. For example, if itformulas described herein are applicable to the.

conditioning of many other types of cellulose derivative yarns such as those composed of or containing cellulose propionate, cellulose butyrate, cellulose acetate propionate, cellulose acetate butyrate, ethyl cellulose, methyl cellulose, benzyl cellulose and others, as well as to the conditioning of silk, wool, cotton, viscose "and other natural or artificial materials.

The term "yam as used herein and in the claims is to be understood as including a single filament, a plurality of-fllaments associated into the form of a thread, either of high or low twist, single or multiple threads associated or twisted together, composite threads composed of a mixtude of natural and artificial filaments or a composite thread formed by twisting together individual strands of natural or artificial materials, as well as cut staple fibers produced from natural and/or artificial filaments or threads and spun yarn produced from such staple fibers.

As indicated above, the yarn conditioning agents of our invention are exceptionally good solvents for a wide variety of mineral, blown and unblown, drying and semi-drying animal and vegetable oils such as cottonseed, olive, castor, neats-foot, sperm and otheroils. This enables them to be used with any of such oils in making up a variety of yarn treating formulas of varying composition.

The yarn conditioning method and compositions of our invention possess many outstanding advantages. The fundamental and outstanding characteristic of the agents employed in accordance with the invention is their ability to deelectrify yarns, especially those composed of or containing organic derivatives of cellulose such as cellulose acetate and render them amenable to various textile operations, especially operations such as those involved in the manufacture of cut staple fibers and in weaving and knitting. Another outstanding characteristic of these compounds is their exceptional solvent power for a wide variety of mineral, animal, and vegetable oils and their ability to act as lubrieating assistants in conjunction with these oils when applied to such yarns. In addition, due to their solubility in water, they may be readily removed from yarns and fabrics by means of the usual aqueous scour baths. By employing the yarn conditioning agents and method of our invention as herein described, one is enabled to obtain highly satisfactory results in the manufacture of yarns and woven fabrics and especially the production from" these yarns of closely knit fabrics free from defects such as pin holes, stitch distortion, Iaddering and the like.

, position containing as where m, y, z and A are, in each instance, a. number not over 2 and B is a number, including 0, not over 2; R and R are substituents selected from the group consisting of hydrogen, alkyl, cycloalkyl and heterocyclic groups, and Ac is any acid group.

2. The process of conditioning yarn composed of or containing'organic derivatives of cellulose to render it more amenable to textile operations including knitting, weaving, spinning, the manufacture of staple fibers, and the like, which comprises applying thereto a lubricating and antistatic composition containing as its essential lu- 1 bricating and anti-static component a salt of a ketonic amine having the general formula:

where 2:, 2/, z and A are, in each instance, a numher not over 2 and B is a number, including 0, not over 2; R and R are substituents selected from the,.group consisting of hydrogen, alkyl, cycloalkyl and heterocyclic groups, and Ac is an acid group.

3. The process of conditioning yarn composed of or containing cellulose acetate to render it more amenable to textile operations including knitting, weaving, spinning, the manufacture of staple fibers, and the like, which comprises ap- -plying thereto a lubricating and anti-static composition containing as its essential lubrieating and anti-static component a salt of a ketonic amine having the general formula:

where x, y, 2, and A are, in each instance, a numher not over 2 and B is a number, including 0, not over 2; R and R are substituents selected from the group consisting of hydrogen, alkyl, cycloalkyl and heterocyclic groups, and Ac is an acid group.

4. The process of conditioning yarn composed of or containing cellulose acetate to render it more amenable to textile operations including knitting, weaving, spinning, the manufacture of staple fibers, and the like, which comprises applying thereto .a lubricating and anti-static comits essential lubricating and anti-static component a salt 'of a ketonic amine having the general formula:

where x, y, z and A are, in each instance, a number not over 2 and B is a number, including 0, I

not over 2; R and R are substituents selected from the group consisting of hydrogen, alkyl, cycloalkyl and heterocyclic groups, and a textile lubricant, and Ac is an acid group.

5. The process of conditioning yarn composed of or containing cellulose acetate to render it more amenable to textile operations including knitting, weaving, spinning, the manufacture of staple fibers, and the like, which comprises applying a lubricating and anti-static composition containing as its essential lubricating and anti-static component diacetone amine oleate.

6. The process of conditioning yamcomposed of or containing cellulose acetate to render it more amenable to textile operations including knitting, weaving, spinning, the manufacture of staple fibers, and the like, which comprises applying a lubricating and anti-static composition containing as its essential lubricating and antistatic component triacetone amine ricinoleate.

7. The process of conditioning yarn composed of or containing cellulose acetate to render it more amenable to textile operations including knitting, weaving, spinning, the manufacture of staple fibers, and the like, which comprises applying a lubricating and anti-static composition containing as its essential lubricating and antistatic component ,B-diethylamino methyl decyl ketone tetrahydrofuroate. 4

8. Textile yarns amenable to textile operations including knitting, weaving, spinning, the manufacture of staple fibers, and the like, impregnated with a lubricating and anti-static composition containing as its essential lubricating and anti-static component a salt of a ketonic amine having the general formula:

where x, 1!, z and A- are, in each instance, a number not over 2 and B is a number, including 0, not over 2; R and R are substituents selected from the group consisting of hydrogen, alkyl, cycloalkyl and heterocyclic groups, and Ac is an acid group.

9. Textile yarns composed of or containing organic derivatives of cellulose amenable to textile operations including knitting, weaving, spinning, the manufacture of staple fibers, and the like, impregnated with a conditioning comprising a salt of a ketonic amine having the general formula:

N N A (11 R '3 (n R)'i where as, y, z and A are, in each instance, a number not over 2 and B is a number, including 0, not over 2; R and R are substituents selected from the group consisting of hydrogen, alkyl, cycloalkyl and heterocyclic groups, and Ac is an acid group.

10. Textile yarns composed of or containing organic derivatives of cellulose amenable to textile operations including knitting, weaving, spinning, the manufacture of staple fibers, and the like, impregnated with a conditioning agent comprising a salt of a, ketonic amine having the general formula: I

number not over 2 and B is a number, including 0, not over 2; R and R are substituents selected from the group consisting of hydrogen, alkyl,

cycloalkyl and heterocyclic groups, and a textile lubricant, and Ac is an acid group.

11. Textile yarns composed of or containing cellulose acetate amenable to textile operations including knitting, weaving, spinning, the manuiacture of staple fibers, and the like, impregnated with a lubricating and anti-static com-. position comprising diacetone amine oleate.

12. Textile yarns composed of or containing cellulose acetate amenable to textile operations including knitting, weaving, spinning, the manufacture of staple fibers, and the like, impregnated with a lubricating and anti-static composition comprising triacetone amine rlcinoleate.

13. Textile yarns composed of or containing cellulose acetate amenable to textile operations including knitting, weaving, spinning, the manuiacture of staple fibers, and the like, impregnated with a lubricating and anti-static composition comprising p-diethylamino methyl decyl ketone tetrahydroifuroate.

JAMES G. MCNAILY. JOSEPH B. DICKEY.

Certificate of Correction Patent No. 2,253,081. August 19, 1941. JAMES G. MGNALLY ET AL.

It is hereby certified that error appears in the printed specification of the above numbered patent requiring correction as follows: Page 4, second column, lines 10-14, claim 1, for that portion of the formula reading It )A (111 Ri N (R/ a)? and that the said Letters Patent should be read with this correction therein that the same may conform to the record of the case in the Patent Oflice.

Signed and sealed this 28th day of October, A. D. 194:1.

read

HENRY VAN ARSDALE,

Acting Gammz'ssz'oner of Patents. 

